Diastereoselective synthesis of 6-bromo-6-(1-hydroxyethyl)penicillanate by cross-coupling of 6,6-dibromopenicillanate and acetaldehyde pronmoted with grgnard reagents: Role of amine ligands

Manabu Kuroboshi, Keiko Mesaki, Syoichi Tateyama, Hideo Tanaka

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Grignard reagent-promoted coupling reaction of diphenylmethyl 6,6-dibromopenicillanate lb with acetaldehyde in the presence of N,N,N',N",N"-pentamethyldiethylenetriamine took place in a highly diastereoselective manner to give diphenylmethyl (1′R,3S,5R,6S)-6- bromo-6-(l′-hydroxyethyl)penicillanate 2b effectively, which is a potent intermediate for the synthesis of carbapenem antibiotics.

Original languageEnglish
Pages (from-to)877-882
Number of pages6
JournalHeterocycles
Volume73
Issue numberC
DOIs
Publication statusPublished - Dec 1 2007

Keywords

  • 6,6-Dibromopenicillanate
  • 6-Bromo-6-(1-hydroxythyl)penicillanate
  • Amine ligand
  • Coupling reaction
  • β-Lactam antibiotic

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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